Sodium Iodide → Iodomethyl 2-(1-(tert-butoxycarbonyl)-4-piperidyl)-ethyl carbonate

HRID 852339

Reaktionsgleichung

Reaktionsgleichung von HRID 852339
[C:1](=[O:21])([O:5][CH2:6][CH2:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]1)[O:2][CH2:3]Cl.[I-:22].[Na+]>CC(C)=O>[C:1](=[O:21])([O:5][CH2:6][CH2:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]1)[O:2][CH2:3][I:22]

Komponenten

4

Edukt 2

HCID 5238Sodium IodideHCID 69348251Chloromethyl 2-(1-(tert-butoxycarbonyl)-4-piperidyl)-ethyl carbonate

Produkt 1

HCID 69576965Iodomethyl 2-(1-(tert-butoxycarbonyl)-4-piperidyl)-ethyl carbonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

Chloromethyl 2-(1-(tert-butoxycarbonyl)-4-piperidyl)-ethyl carbonate (4.9 g) was added to a solution of sodium iodide (9 g) in acetone (20 ml). After stirring at 40° C. for 2.5 hours the reaction mixture was cooled to room temperature, filtered and evaporated in vacuo. The residue was taken up in dichloromethane, washed with aqueous sodium bicarbonate and sodium thiosulfate, dried over magnesium sulfate, filtered and evaporated in vacuo. Purification on silica gel with hexane/ethyl acetate (2:1) as eluent gave the title compound as a light yellow oil.

Aufarbeitung

  1. temperaturewas cooled to room temperature
  2. filtrationfiltered
  3. customevaporated in vacuo
  4. washwashed with aqueous sodium bicarbonate and sodium thiosulfate
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customPurification on silica gel with hexane/ethyl acetate (2:1) as eluent

Quellen und Nachweise

ORD-Eintrag
ord-44233d549d1e400681905d6d8b37cd8b
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07253193B2

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